The present invention relates to novel cyclohexenonedioxothiochromanoyl derivatives of the formula I, 
where:
X is oxygen, sulfur, Sxe2x95x90O, S(xe2x95x90O)2, CR4R5, Cxe2x95x90O or Cxe2x95x90NR6;
R1 is hydrogen, nitro, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, aminosulfonyl, Nxe2x80x94(C1-C6-alkyl)aminosulfonyl, N,N-di(C1-C6-alkyl)aminosulfonyl, Nxe2x80x94(C1-C6-alkylsulfonyl)amino, Nxe2x80x94(C1-C6-haloalkylsulfonyl)amino, Nxe2x80x94(C1-C6-alkyl)-Nxe2x80x94(C1-C6-alkylsulfonyl)amino or Nxe2x80x94(C1-C6-alkyl)-Nxe2x80x94(C1-C6-haloalkylsulfonyl)amino;
R2 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
R3 is hydrogen, C1-C6-alkyl or halogen;
R4, R5 are hydrogen, nitro, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, Nxe2x80x94C1-C6-alkylamino, Nxe2x80x94C1-C6-haloalkylamino, N,N-di(C1-C6-alkyl)amino, Nxe2x80x94C1-C6-alkoxyamino, Nxe2x80x94(C1-C6-alkoxy)-Nxe2x80x94(C1-C6-alkyl)amino, 1-tetra-hydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl; or
R4 and R5 together form an xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94Sxe2x80x94 or xe2x80x94Oxe2x80x94(CH2)nxe2x80x94 chain which may be substituted by one to three radicals selected from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
R4 and R5 together form a xe2x80x94(CH2)pxe2x80x94 chain which may be interrupted by oxygen or sulfur and/or may be substituted by one to four radicals selected from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
R4 and R5 together form a methylidene group which may be substituted by one or two radicals selected from the following group:
halogen, hydroxyl, formyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl or C1-C6-haloalkylsulfonyl;
R6 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
l is 0 to 4;
m is 2 to 4;
n is 1 to 5;
p is 2 to 5;
R7 is a compound IIa or IIb 
xe2x80x83where
R8 is halogen, OR10, SR10, SOR11, SO2R11, OSO2R11, POR11R12, OPOR11R12, OPSR11R12, NR13R14, ONR14R14, N-bonded heterocyclyl or Oxe2x80x94(N-bonded heterocyclyl), where the heterocyclyl radical of the two lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R9 is nitro, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, di(C1-C6-alkoxy)methyl, di(C1-C6-alkylthio)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio)methyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl or C1-C6-haloalkoxycarbonyl; or
two radicals R9 which are attached to the same carbon together form an xe2x80x94Oxe2x80x94(CH2)mOxe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94Sxe2x80x94 or xe2x80x94Oxe2x80x94(CH2)nxe2x80x94 chain which may be substituted by one to three radicals selected from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
two radicals R9 which are attached to the same carbon together form a xe2x80x94(CH2)pxe2x80x94 chain which may be interrupted by oxygen or sulfur and/or may be substituted by one to four radicals selected from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
two radicals R9 which are attached to the same carbon together form a methylidene group which may be substituted by one to two radicals selected from the following group:
halogen, hydroxyl, formyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl; or
two radicals R9 which are attached to the same carbon together with this carbon form a carbonyl group; or
two radicals R9 which are attached to different carbons together form a xe2x80x94(CH2)nxe2x80x94 chain which may be substituted by one to three radicals selected from the following group:
halogen, C1-C6-alkyl, C1-C6-alkoxy, hydroxyl or C1-C6-alkoxycarbonyl;
R10 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C1-C20-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkynyloxycarbonyl, C1-C6-alkylthiocarbonyl, C1-C6-alkylaminocarbonyl, C3-C6-alkenylaminocarbonyl, C3-C6-alkynylaminocarbonyl, N,N-di(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C3-C6-alkenyl)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C3-C6-alkynyl)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C1-C6-alkoxy)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C3-C6-alkenyl)-Nxe2x80x94(C1-C6-alkoxy)aminocarbonyl, N-(C3-C6-alkynyl)-Nxe2x80x94(C1-C6-alkoxy)aminocarbonyl, di-(C1-C6-alkyl)aminothiocarbonyl, C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-alkoxyimino-C1-C6-alkyl, Nxe2x80x94(C1-C6-alkylamino)imino-C1-C6-alkyl or N,N-di-(C1-C6-alkylamino)imino-C1-C6-alkyl, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, di-(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxy-C1-C4-alkoxycarbonyl, di-(C1-C4-alkyl)amino-C1-C4-alkoxycarbonyl, hydroxycarbonyl, C1-C4-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl, aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
xe2x80x83is phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, phenylaminocarbonyl, Nxe2x80x94(C1-C6-alkyl)-N-(phenyl)aminocarbonyl, heterocyclylaminocarbonyl, Nxe2x80x94(C1-C6-alkyl)-N-(heterocyclyl)aminocarbonyl, phenyl-C2-C6-alkenylcarbonyl or heterocyclyl-C2-C6-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R11, R12 are C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, hydroxyl, C1-C6-alkoxy, amino, C1-C6-alkylamino, C1-C6-haloalkylamino, di-(C1-C6-alkyl)amino or di-(C1-C6-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, di-(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxy-C1-C4-alkoxycarbonyl, di-(C1-C4-alkyl)aminno-C1-C4-alkoxycarbonyl, hydroxycarbonyl, C1-C4-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl, aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
xe2x80x83are phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
xe2x80x83R13 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C6-alkylamino, di-(C1-C6-alkyl)amino or C1-C6-alkylcarbonylamino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals selected from the following group:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, di-(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxy-C1-C4-alkoxycarbonyl, di-(C1-C4-alkyl)amino-C1-C4-alkoxycarbonyl, hydroxycarbonyl, C1-C4-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl, aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
xe2x80x83is phenyl, heterocyclyl, phenyl-C1-C6-alkyl or heterocyclyl-C1-C6-alkyl, where the phenyl or heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R14 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C1-C6-alkylcarbonyl;
q is 0 to 6
and agriculturally useful salts thereof.
The invention additionally relates to processes for preparing compounds of the formula I, to compositions comprising them and to the use of these derivatives or of compositions comprising them for controlling harmful plants.
Dioxothiochroman derivatives which are linked to a (1-hydroxy-3-oxocyclohex-1-en-2-yl)carbonyl radical with or without substitution are known from the literature, for example from DE-A 19 532 311 and WO 97/08164. However, the herbicidal properties of the prior art compounds and their compatibility with crop plants are not entirely satisfactory.
It is an object of the present invention to provide novel biologically, in particular herbicidally, active ingredients having improved properties.
We have found that this object is achieved by the cyclohexenonedioxothiochromanoyl derivatives of the formula I and their herbicidal action.
Furthermore, the invention provides herbicidal compositions comprising the compounds I and having very good herbicidal activity. Additionally, the invention provides processes for preparing these compositions and methods for controlling undesirable plant growth using the compounds I.
Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers and, if this is the case, be present as enantiomers or mixtures of diastereomers. The invention provides both pure enantiomers or diastereomers and mixtures thereof.
The compounds of the formula I may also be present in the form of their agriculturally useful salts, the kind of salt generally not being important. The salts of those cations or the acid addition salts of those acids whose cations or anions, respectively, do not adversely affect the herbicidal activity of the compounds I are generally suitable.
Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium where, if desired, one to four hydrogen atoms may be replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, and furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
The organic molecular moieties mentioned for the substituents R1-R14 or as radicals on phenyl and heterocyclyl radicals represent collective terms for individual listings of the individual group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, halo-alkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, N-alkylaminosulfonyl, N,N-dialkylaminosulfonyl, N-alkylamino, N,N-dialkyl-amino, N-haloalkylamino, N-alkoxyamino, N-alkoxy-N-alkylamino, N-alkylcarbonylamino, N-alkylsulfonylamino, N-haloalkylsulfonylamino, N-alkyl-N-alkylsulfonylamino, N-alkyl-N-haloalkylsulfonylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylthiocarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, alkoxyalkyl, dialkoxymethyl, dialkylthiomethyl, (alkoxy)(alkylthio)methyl, alkylcarbonylalkyl, alkoxyiminoalkyl, N-(alkylamino)iminoalkyl, N-(dialkylamino)iminoalkyl, phenylalkenylcarbonyl, heterocyclylalkenylcarbonyl, N-alkoxy-N-alkyl aminocarbonyl, N-alkyl-N-phenylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl, dialkylaminoalkoxycarbonyl, alkoxyalkoxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, alkenylaminocarbonyl, N-alkenyl-N-alkylaminocarbonyl, N-alkenyl-N-alkoxyaminocarbonyl, alkynylcarbonyl, alkynyloxycarbonyl, alkynylaminocarbonyl, N-alkynyl-N-alkylaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkynyloxy and alkoxyalkoxy moieties may be straight-chain or branched. Unless stated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. Halogen is in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:
C1-C4-alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;
C1-C6-alkyl, and the alkyl moieties of C1-C6-alkoxyimino-C1-C6-alkyl, Nxe2x80x94(C1-C6-alkylamino)imino-C1-C6-alkyl, N-(di-C1-C6-alkylamino)imino-C1-C6-alkyl, Nxe2x80x94(C1-C6-alkoxy)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C3-C6-alkenyl)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, (C3-C6-alkynyl)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C1-C6-alkyl)-N-phenylaminocarbonyl, Nxe2x80x94(C1-C6-alkyl)-N-heterocyclylaminocarbonyl, phenyl-C1-C6-alkyl, Nxe2x80x94(C1-C6-alkyl)-Nxe2x80x94(C1-C6-alkylsulfonyl)amino, Nxe2x80x94(C1-C6-alkyl)-Nxe2x80x94(C1-C6-haloalkylsulfonyl)amino, heterocyclyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl: C1-C4-alkyl, as mentioned above, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;
C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;
C1-C6-haloalkyl, and the haloalkyl moieties of Nxe2x80x94C1-C6-haloalkylamino: C1-C4-haloalkyl as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;
C1-C4-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;
C1-C6-alkoxy, and the alkoxy moieties of Nxe2x80x94C1-C6-alkoxyamino, di(C1-C6-alkoxy)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio)methyl, C1-C6-alkoxyimino-C1-C6-alkyl, Nxe2x80x94(C1-C6-alkoxy)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C3-C6-alkenyl)-Nxe2x80x94(C1-C6-alkoxy)aminocarbonyl and Nxe2x80x94(C3-C6-alkynyl)-Nxe2x80x94(C1-C6-alkoxy)aminocarbonyl: C1-C4-alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
C16-haloalkoxy: C14-haloalkoxy as mentioned above, and also, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
C1-C4-alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio;
C1-C6-alkylthio and the alkylthio moieties of C1-C6-alkylthiocarbonyl, di-(C1-C6-alkylthio)methyl and (C1-C6-alkoxy)(C1-C6-alkylthio)methyl: C1-C4-alkylthio as mentioned above, and also, for example pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;
C1-C4-haloalkylthio: a C1-C4-alkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio;
C1-C6-haloalkylthio: C1-C4-haloalkylthio as mentioned above, and also, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio;
C1-C6-alkylsulfinyl (C1-C6-alkyl-S(xe2x95x90O)xe2x80x94): for example methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;
C1-C6-haloalkylsulfinyl: a C1-C6-alkylsulfinyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl, 1-(fluoromethyl)-2-fluoroethylsulfinyl, 1-(chloromethyl)-2-chloroethylsulfinyl, 1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl, nonafluoro-butylsulfinyl, 5-fluoropentylsulfinyl, 5-chloropentyl-sulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chloro-hexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;
C1-C6-alkylsulfonyl (C1-C6-alkyl-S(xe2x95x90O)2xe2x80x94), and the alkylsulfonyl radicals of Nxe2x80x94(C1-C6-alkylsulfonyl)amino and Nxe2x80x94(C1-C6-alkyl)-Nxe2x80x94(C1-C6-alkylsulfonyl)amino: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl;
C1-C6-haloalkylsulfonyl, and the haloalkyl radicals of Nxe2x80x94(C1-C6-haloalkylsulfonyl)amino and Nxe2x80x94(C1-C6-alkyl)-Nxe2x80x94(C1-C6-haloalkylsulfonyl)amino: a C1-C6-alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutyl-sulfonyl, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl;
C1-C6-alkylamino, and the alkylamino radicals of Nxe2x80x94(C1-C6-alkylamino)imino-C1-C6-alkyl, i.e. for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;
(C1-C4-alkylamino)sulfonyl: for example methylaminosulfonyl, ethylaminosulfonyl, propylaminosulfonyl, 1-methylethylaminosulfonyl, butylaminosulfonyl, 1-methylpropylaminosulfonyl, 2-methylpropylaminosulfonyl or 1,1-dimethylethylaminosulfonyl;
(C1-C6-alkylamino)sulfonyl: (C1-C4-alkylamino)sulfonyl as mentioned above, and also, for example, pentylaminosulfonyl, 1-methylbutylaminosulfonyl, 2-methylbutylaminosulfonyl, 3-methylbutylaminosulfonyl, 2,2-dimethylpropylaminosulfonyl, 1-ethylpropylaminosulfonyl, hexylaminosulfonyl, 1,1-dimethylpropylaminosulfonyl, 1,2-dimethylpropylaminosulfonyl, 1-methylpentylaminosulfonyl, 2-methylpentylaminosulfonyl, 3-methylpentylaminosulfonyl, 4-methylpentylaminosulfonyl, 1,1-dimethylbutylaminosulfonyl, 1,2-dimethylbutylaminosulfonyl, 1,3-dimethylbutylaminosulfonyl, 2,2-dimethylbutylaminosulfonyl, 2,3-dimethylbutylaminosulfonyl, 3,3-dimethylbutylaminosulfonyl, 1-ethylbutylaminosulfonyl, 2-ethylbutylaminosulfonyl, 1,1,2-trimethylpropylaminosulfonyl, 1,2,2-trimethylpropylaminosulfonyl, 1-ethyl-1-methylpropylaminosulfonyl or 1-ethyl-2-methylpropylaminosulfonyl;
di(C1-C4-alkyl)aminosulfonyl: for example N,N-dimethylaminosulfonyl, N,N-diethylaminosulfonyl, N,N-di(1-methylethyl)aminosulfonyl, N,N-dipropylaminosulfonyl, N,N-dibutylaminosulfonyl, N,N-di(1-methylpropyl)aminosulfonyl, N,N-di(2-methylpropyl)aminosulfonyl, N,N-di(1,1-dimethylethyl)aminosulfonyl, N-ethyl-N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl, N-methyl-N-(1-methylethyl)aminosulfonyl, N-butyl-N-methylaminosulfonyl, N-methyl-N-(1-methylpropyl)aminosulfonyl, N-methyl-N-(2-methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)-N-methylaminosulfonyl, N-ethyl-N-propylaminosulfonyl, N-ethyl-N-(1-methylethyl)aminosulfonyl, N-butyl-N-ethylaminosulfonyl, N-ethyl-N-(1-methylpropyl)aminosulfonyl, N-ethyl-N-(2-methylpropyl)aminosulfonyl, N-ethyl-N-(1,1-dimethylethyl)aminosulfonyl, N-(1-methylethyl)-N-propylaminosulfonyl, N-butyl-N-propylaminosulfonyl, N-(1-methylpropyl)-N-propylaminosulfonyl, N-(2-methylpropyl)-N-propylaminosulfonyl, N-(1,1-dimethylethyl)-N-propylaminosulfonyl, N-butyl-N-(1-methylethyl)aminosulfonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminosulfonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminosulfonyl, N-butyl-N-(1-methylpropyl)aminosulfonyl, N-butyl-N-(2-methylpropyl)aminosulfonyl, N-butyl-N-(1,1-dimethylethyl)aminosulfonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminosulfonyl or N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminosulfonyl;
di(C1-C6-alkyl)aminosulfonyl: di-(C1-C4-alkyl)aminosulfonyl as mentioned above, and also, for example, N-methyl-N-pentylaminosulfonyl, N-methyl-N-(1-methylbutyl)aminosulfonyl, N-methyl-N-(2-methylbutyl)aminosulfonyl, N-methyl-N-(3-methylbutyl)aminosulfonyl, N-methyl-N-(2,2-dimethylpropyl)aminosulfonyl, N-methyl-N-(1-ethylpropyl)aminosulfonyl, N-methyl-N-hexylaminosulfonyl, N-methyl-N-(1,1-dimethylpropyl)aminosulfonyl, N-methyl-N-(1,2-dimethylpropyl)aminosulfonyl, N-methyl-N-(1-methylpentyl)aminosulfonyl, N-methyl-N-(2-methylpentyl)aminosulfonyl, N-methyl-N-(3-methylpentyl)aminosulfonyl, N-methyl-N-(4-methylpentyl)aminosulfonyl, N-methyl-N-(1,1-dimethylbutyl)aminosulfonyl, N-methyl-N-(1,2-dimethylbutyl)aminosulfonyl, N-methyl-N-(1,3-dimethylbutyl)aminosulfonyl, N-methyl-N-(2,2-dimethylbutyl)aminosulfonyl, N-methyl-N-(2,3-dimethylbutyl)aminosulfonyl, N-methyl-N-(3,3-dimethylbutyl)aminosulfonyl, N-methyl-N-(1-ethylbutyl)aminosulfonyl, N-methyl-N-(2-ethylbutyl)aminosulfonyl, N-methyl-N-(1,1,2-trimethylpropyl)aminosulfonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminosulfonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl, N-ethyl-N-pentylaminosulfonyl, N-ethyl-N-(1-methylbutyl)aminosulfonyl, N-ethyl-N-(2-methylbutyl)aminosulfonyl, N-ethyl-N-(3-methylbutyl)aminosulfonyl, N-ethyl-N-(2,2-dimethylpropyl)aminosulfonyl, N-ethyl-N-(1-ethylpropyl)aminosulfonyl, N-ethyl-N-hexylaminosulfonyl, N-ethyl-N-(1,1-dimethylpropyl)aminosulfonyl, N-ethyl-N-(1,2-dimethylpropyl)aminosulfonyl, N-ethyl-N-(1-methylpentyl)aminosulfonyl, N-ethyl-N-(2-methylpentyl)aminosulfonyl, N-ethyl-N-(3-methylpentyl)aminosulfonyl, N-ethyl-N-(4-methylpentyl)aminosulfonyl, N-ethyl-N-(1,1-dimethylbutyl)aminosulfonyl, N-ethyl-N-(1,2-dimethylbutyl)aminosulfonyl, N-ethyl-N-(1,3-dimethylbutyl)aminosulfonyl, N-ethyl-N-(2,2-dimethylbutyl)aminosulfonyl, N-ethyl-N-(2,3-dimethylbutyl)aminosulfonyl, N-ethyl-N-(3,3-dimethylbutyl)aminosulfonyl, N-ethyl-N-(1-ethylbutyl)aminosulfonyl, N-ethyl-N-(2-ethylbutyl)aminosulfonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminosulfonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminosulfonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl, N-propyl-N-pentylaminosulfonyl, N-butyl-N-pentylaminosulfonyl, N,N-dipentylaminosulfonyl, N-propyl-N-hexylaminosulfonyl, N-butyl-N-hexylaminosulfonyl, N-pentyl-N-hexylaminosulfonyl or N,N-dihexylaminosulfonyl;
di(C1-C4-alkyl)amino, and the dialkylamino radicals of di(C1-C4-alkyl)amino-C1-C4-alkoxycarbonyl and N-(di-C1-C4-alkylamino)imino-C1-C6-alkyl, for example N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino, N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;
di(C1-C6-alkyl)amino, and the dialkylamino radicals of di(C1-C6-alkyl)aminoimino-C1-C6-alkyl: di-(C1-C4-alkyl)amino as mentioned above, and also N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino, N-ethyl-N-pentylamino, N-methyl-N-hexylamino or N-ethyl-N-hexylamino;
C1-C4-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1,1-dimethylethylcarbonyl;
C1-C6-alkylcarbonyl, and the alkylcarbonyl radicals of C1-C6-alkylcarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkyl: C1-C4-alkylcarbonyl as mentioned above, and also, for example, pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethyl-propylcarbonyl, hexylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutyl-carbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;
C1-C20-alkylcarbonyl: C1-C6-alkylcarbonyl as mentioned above, and also heptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or heptadecylcarbonyl;
C1-C6-haloalkylcarbonyl: a C1-C6-alkylcarbonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, 1-(fluoromethyl)-2-fluoroethylcarbonyl, 1-(chloromethyl)-2-chloroethylcarbonyl, 1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl, nonafluorobutylcarbonyl, 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5-bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorohexylcarbonyl, 6-chlorohexylcarbonyl, 6-bromohexylcarbonyl or perfluorohexylcarbonyl;
C1-C4-alkoxycarbonyl, and the alkoxycarbonyl moieties of di(C1-C4-alkyl)amino-C1-C4-alkoxycarbonyl: for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;
(C1-C6-alkoxy)carbonyl: (C1-C4-alkoxy)carbonyl as mentioned above, and also, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethyl-butoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl;
C1-C6-haloalkoxycarbonyl: a C1-C4-alkoxycarbonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2,2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl, 2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl, 2,2,3,3,3-pentafluoropropoxycarbonyl, heptafluoropropoxycarbonyl, 1-(fluoromethyl)-2-fluoroethoxycarbonyl, 1-(chloromethyl)-2-chloroethoxycarbonyl, 1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl, 4-iodobutoxycarbonyl, 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonyl or 6-bromohexoxycarbonyl;
(C1-C4-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy, propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or 1,1-dimethylethylcarbonyloxy;
(C1-C4-alkylamino)carbonyl: for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1,1-dimethylethylaminocarbonyl;
(C1-C6-alkylamino)carbonyl: (C1-C4-alkylamino)carbonyl as mentioned above, and also, for example, pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, Hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 1-ethyl-2-methylpropylaminocarbonyl;
di(C1-C4-alkyl)aminocarbonyl: for example N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl, N,N-dibutylaminocarbonyl, N,N-di(1-methylpropyl)aminocarbonyl, N,N-di(2-methylpropyl)aminocarbonyl, N,N-di(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N-(1-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, N-(1,1-dimethylethyl)-N-propylaminocarbonyl, N-butyl-N-(1-methylethyl)aminocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl, N-butyl-N-(1-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)aminocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;
di(C1-C6-alkyl)aminocarbonyl: di-(C1-C4-alkyl)aminocarbonyl as mentioned above, and also, for example, N-methyl-N-pentylaminocarbonyl, N-methyl-N-(1-methylbutyl)aminocarbonyl, N-methyl-N-(2-methylbutyl)aminocarbonyl, N-methyl-N-(3-methylbutyl)aminocarbonyl, N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl, N-methyl-N-(1-ethylpropyl)aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl, N-methyl-N-(1-methylpentyl)aminocarbonyl, N-methyl-N-(2-methylpentyl)aminocarbonyl, N-methyl-N-(3-methylpentyl)aminocarbonyl, N-methyl-N-(4-methylpentyl)aminocarbonyl, N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl, N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl, N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(1-ethylbutyl)aminocarbonyl, N-methyl-N-(2-ethylbutyl)aminocarbonyl, N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl, N-ethyl-N-pentylaminocarbonyl, N-ethyl-N-(1-methylbutyl)aminocarbonyl, N-ethyl-N-(2-methylbutyl)aminocarbonyl, N-ethyl-N-(3-methylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1-ethylpropyl)aminocarbonyl, N-ethyl-N-hexylaminocarbonyl, N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1-methylpentyl)aminocarbonyl, N-ethyl-N-(2-methylpentyl)aminocarbonyl, N-ethyl-N-(3-methylpentyl)aminocarbonyl, N-ethyl-N-(4-methylpentyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1-ethylbutyl)aminocarbonyl, N-ethyl-N-(2-ethylbutyl)aminocarbonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl, N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl, N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl, N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or N,N-dihexylaminocarbonyl;
di(C1-C6-alkyl)aminothiocarbonyl: for example N,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl, N,N-di(1-methylethyl)aminothiocarbonyl, N,N-dipropylaminothiocarbonyl, N,N-dibutylaminothiocarbonyl, N,N-di(1-methylpropyl)aminothiocarbonyl, N,N-di(2-methylpropyl)aminothiocarbonyl, N,N-di(1,1-dimethylethyl)aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N-methyl-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N-methyl-N-(1-methylpropyl)aminothiocarbonyl, N-methyl-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-ethylaminothiocarbonyl, N-ethyl-N-(1-methylpropyl)aminothiocarbonyl, N-ethyl-N-(2-methylpropyl)aminothiocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminothiocarbonyl, N-(1-methylethyl)-N-propylaminothiocarbonyl, N-butyl-N-propylaminothiocarbonyl, N-(1-methylpropyl)-N-propylaminothiocarbonyl, N-(2-methylpropyl)-N-propylaminothiocarbonyl, N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl, N-butyl-N-(1-methylethyl)aminothiocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-(1-methylpropyl)aminothiocarbonyl, N-butyl-N-(2-methylpropyl)aminothiocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl, N-methyl-N-pentylaminothiocarbonyl, N-methyl-N-(1-methylbutyl)aminothiocarbonyl, N-methyl-N-(2-methylbutyl)aminothiocarbonyl, N-methyl-N-(3-methylbutyl)aminothiocarbonyl, N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethylpropyl)aminothiocarbonyl, N-methyl-N-hexylaminothiocarbonyl, N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-methylpentyl)aminothiocarbonyl, N-methyl-N-(2-methylpentyl)aminothiocarbonyl, N-methyl-N-(3-methylpentyl)aminothiocarbonyl, N-methyl-N-(4-methylpentyl)aminothiocarbonyl, N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(2,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1-ethylbutyl)aminothiocarbonyl, N-methyl-N-(2-ethylbutyl)aminothiocarbonyl, N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl, N-ethyl-N-pentylaminothiocarbonyl, N-ethyl-N-(1-methylbutyl)aminothiocarbonyl, N-ethyl-N-(2-methylbutyl)aminothiocarbonyl, N-ethyl-N-(3-methylbutyl)aminothiocarbonyl, N-ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl, N-ethyl-N-hexylaminothiocarbonyl, N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-methylpentyl)aminothiocarbonyl, N-ethyl-N-(2-methylpentyl)aminothiocarbonyl, N-ethyl-N-(3-methylpentyl)aminothiocarbonyl, N-ethyl-N-(4-methylpentyl)aminothiocarbonyl, N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl, N-ethyl-N-(2-ethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl, N-propyl-N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl, N,N-dipentylaminothiocarbonyl, N-propyl-N-hexylaminothiocarbonyl, N-butyl-N-hexylaminothiocarbonyl, N-pentyl-N-hexylaminothiocarbonyl or N,N-dihexylaminothiocarbonyl;
C1-C4-alkoxy-C1-C4-alkyl: C1-C4-alkyl which is substituted by C1-C4-alkoxy as mentioned above, i.e., for example, methoxymethyl, ethoxymethyl, propoxymethyl, (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl;
C1-C4-alkoxy-C1-C4-alkoxy, and the alkoxyalkoxy moieties of C1-C4-alkoxy-C1-C4-alkoxycarbonyl: C1-C4-alkoxy which is substituted by C1-C4-alkoxy as mentioned above, i.e., for example, methoxymethoxy, ethoxymethoxy, propoxymethoxy, (1-methylethoxy)methoxy, butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, (1,1-dimethylethoxy)methoxy, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(propoxy)propoxy, 2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy, 2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy, 2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy, 3-(propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy, 3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy, 3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy, 2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(butoxy)butoxy, 2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy, 3-(propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy, 3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy, 3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy, 4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(butoxy)butoxy, 4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy or 4-(1,1-dimethylethoxy)butoxy;
C3-C6-alkenyl, and the alkenyl moieties of C3-C6-alkenylcarbonyl, C3-C6-alkenyloxy, C3-C6-alkenyloxycarbonyl, C3-C6-alkenylaminocarbonyl, Nxe2x80x94(C3-C6-alkenyl)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C3-C6-alkenyl )-Nxe2x80x94(C1-C6-alkoxy)aminocarbonyl: for example prop-2-en-1-yl, but-1-en-4-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, 2-buten-1-yl, 1-penten-3-yl, 1-penten-4-yl, 2-penten-4-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl;
C2-C6-alkenyl, and the alkenyl moieties of C2-C6-alkenylcarbonyl, phenyl-C2-C6-alkenylcarbonyl and heterocyclyl-C2-C6-alkenylcarbonyl: C3-C6-alkenyl as mentioned above, and also ethenyl;
C3-C6-haloalkenyl: a C3-C6-alkenyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;
C3-C6-alkynyl, and the alkynyl moieties of C3-C6-alkynylcarbonyl, C3-C6-alkynyloxy, C3-C6-alkynyloxycarbonyl, C3-C6-alkynylaminocarbonyl, Nxe2x80x94(C3-C6-alkynyl)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C36-alkynyl)-Nxe2x80x94(C1-C6-alkoxy)aminocarbonyl: for example propargyl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl;
C2-C6-alkynyl, and the alkynyl moieties of C2-C6-alkynylcarbonyl: C3-C6-alkynyl as mentioned above, and also ethynyl;
C3-C6-haloalkynyl: a C3-C6-alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;
C3-C6-cycloalkyl, and the cycloalkyl moieties of C3-C6-cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
heterocyclyl, and the heterocyclyl moieties of heterocyclylcarbonyl, heterocyclyl-C1-C6-alkyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylcarbonyl-C1-C6-alkyl, Nxe2x80x94(C1-C6-alkyl)-N-(heterocyclyl)aminocarbonyl, heterocyclylaminocarbonyl: a saturated, partially saturated or unsaturated 5- or 6-membered heterocyclic ring which is attached via carbon and contains one to four identical or different heteroatoms selected from the following group: oxygen, sulfur or nitrogen, i.e., for example, 5-membered rings having one heteroatom:
tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl, 2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl, 2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl, 4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl, 3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl, 3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl or pyrrol-3-yl;
5-membered rings having 2 heteroatoms such as:
tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl, 1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl, 1,2-dithiolan-3-yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl, tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl, tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl, 2,5-dihydro-1H-pyrazol-3-yl, 2,5-dihydro-1H-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxa-zol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, xcex943-1,2-dithiol-3-yl, xcex943-1,2-dithiol-4-yl, xcex943-1,2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl, 4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl, 2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl, 2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H-imidazol-2-yl, 2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl, 1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl or thiazol-5-yl;
5-membered rings having 3 heteroatoms such as: 1,2,3-xcex942-oxadiazolin-4-yl, 1,2,3-xcex942-oxadiazolin-5-yl, 1,2,4-xcex944-oxadiazolin-3-yl, 1,2,4-xcex944-oxadiazolin-5-yl, 1,2,4-xcex942-oxadiazolin-3-yl, 1,2,4-xcex942-oxadiazolin-5-yl, 1,2,4-xcex943-oxadiazolin-3-yl, 1,2,4-xcex943-oxadiazolin-5-yl, 1,3,4-xcex942-oxadiazolin-2-yl, 1,3,4-xcex942-oxadiazolin-5-yl, 1,3,4-xcex943-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl, 1,2,4-xcex944-thiadiazolin-3-yl, 1,2,4-xcex944-thiadiazolin-5-yl, 1,2,4-xcex943-thiadiazolin-3-yl, 1,2,4-xcex943-thiadiazolin-5-yl, 1,2,4-xcex942-thiadiazolin-3-yl, 1,2,4-xcex942-thiadiazolin-5-yl, 1,3,4-xcex942-thiadiazolin-2-yl, 1,3,4-xcex942-thiadiazolin-5-yl, 1,3,4-xcex943-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl, 1,3,2-dioxathiolan-4-yl, 1,2,3-xcex942-triazolin-4-yl, 1,2,3-xcex942-triazolin-5-yl, 1,2,4-xcex942-triazolin-3-yl, 1,2,4-xcex942-triazolin-5-yl, 1,2,4-xcex943-triazolin-3-yl, 1,2,4-xcex943-triazolin-5-yl, 1,2,4-xcex941-triazolin-2-yl, 1,2,4-triazolin-3-yl, 3H-1,2,4-dithiazol-5-yl, 2H-1,3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl, 1,2,3-triazol-4-yl or 1,2,4-triazol-3-yl;
5-membered rings having 4 heteroatoms such as: tetrazol-5-yl,
6-membered rings having one heteroatom such as:
tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl, 2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl, 1,2,3,4-tetrahydropyridin-5-yl, 1,2,3,4-tetrahydropyridin-4-yl, 1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2-yl, 2H-5,6-dihydropyran-2-yl, 2H-5,6-dihydropyran-3-yl, 2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl, 2H-5,6-dihydropyran-6-yl, 2H-5,6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl, 2H-5,6-dihydrothiopyran-5-yl, 2H-5,6-dihydrothiopyran-6-yl, 1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl, 1,2,5,6-tetrahydropyridin-4-yl, 1,2,5,6-tetrahydropyridin-5-yl, 1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl, 2,3,4,5-tetrahydropyridin-3-yl, 2,3,4,5-tetrahydropyridin-4-yl, 2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl, 4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl, 1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl, 1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl, 1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl, 3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl, 3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl, 3,4-di-hydropyridin-6-yl, 2,5-dihydropyridin-2-yl, 2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl, 2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl, 2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl, 2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl, 2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl;
6-membered rings having two heteroatoms such as:
1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, 1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-4-yl, tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl, tetrahydro-1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,2-oxazin-3-yl, tetrahydro-1,2-oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl, tetrahydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-oxazin-3-yl, 2H-5,6-dihydro-1,2-oxazin-4-yl, 2H-5,6-dihydro-1,2-oxazin-5-yl, 2H-5,6-dihydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-thiazin-3-yl, 2H-5,6-dihydro-1,2-thiazin-4-yl, 2H-5,6-dihydro-1,2-thiazin-5-yl, 2H-5,6-dihydro-1,2-thiazin-6-yl, 4H-5,6-dihydro-1,2-oxazin-3-yl, 4H-5,6-dihydro-1,2-oxazin-4-yl, 4H-5,6-dihydro-1,2-oxazin-5-yl, 4H-5,6-dihydro-1,2-oxazin-6-yl, 4H-5,6-dihydro-1,2-thiazin-3-yl, 4H-5,6-dihydro-1,2-thiazin-4-yl, 4H-5,6-dihydro-1,2-thiazin-5-yl, 4H-5,6-dihydro-1,2-thiazin-6-yl, 2H-3,6-dihydro-1,2-oxazin-3-yl, 2H-3,6-dihydro-1,2-oxazin-4-yl, 2H-3,6-dihydro-1,2-oxazin-5-yl, 2H-3,6-dihydro-1,2-oxazin-6-yl, 2H-3,6-dihydro-1,2-thiazin-3-yl, 2H-3,6-dihydro-1,2-thiazin-4-yl, 2H-3,6-dihydro-1,2-thiazin-5-yl, 2H-3,6-dihydro-1,2-thiazin-6-yl, 2H-3,4-dihydro-1,2-oxazin-3-yl, 2H-3,4-dihydro-1,2-oxazin-4-yl, 2H-3,4-dihydro-1,2-oxazin-5-yl, 2H-3,4-dihydro-1,2-oxazin-6-yl, 2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4-dihydro-1,2-thiazin-4-yl, 2H-3,4-dihydro-1,2-thiazin-5-yl, 2H-3,4-dihydro-1,2-thiazin-6-yl, 2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4-yl, 2,3,4,5-tetrahydropyridazin-5-yl, 2,3,4,5-tetrahydropyridazin-6-yl, 3,4,5,6-tetrahydropyridazin-3-yl, 3,4,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-3-yl, 1,2,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-5-yl, 1,2,5,6-tetrahydropyridazin-6-yl, 1,2,3,6-tetrahydropyridazin-3-yl, 1,2,3,6-tetrahydropyridazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5,6-dihydro-1,3-oxazin-6-yl, 4H-5,6-dihydro-1,3-thiazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-4-yl, 4H-5,6-dihydro-1,3-thiazin-5-yl, 4H-5,6-dihydro-1,3-thiazin-6-yl, 3,4,5,6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl, 3,4,5,6-tetrahydropyrimidin-5-yl, 3,4,5,6-tetrahydropyrimidin-6-yl, 1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3,4-tetrahydropyrazin-5-yl, 1,2,3,4-tetrahydropyrimidin-2-yl, 1,2,3,4-tetrahydropyrimidin-4-yl, 1,2,3,4-tetrahydropyrimidin-5-yl, 1,2,3,4-tetrahydropyrimidin-6-yl, 2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl, 2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl, 2H-1,2-oxazin-3-yl, 2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl, 2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl, 2H-1,2-thiazin-5-yl, 2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl, 4H-1,2-oxazin-4-yl, 4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl, 4H-1,2-thiazin-3-yl, 4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl, 4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl, 6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl, 6H-1,2-thiazin-4-yl, 6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl, 2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl, 2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl, 2H-1,3-thiazin-5-yl, 2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl, 4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl, 4H-1,3-thiazin-2-yl, 4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl, 4H-1,3-thiazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl, 2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl, 2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl, 2H-1,4-thiazin-5-yl, 2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1,4-oxazin-3-yl, 4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl, 1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl, 1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl, 1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl, 1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl, 1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl, 1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl, 1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or 3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl or pyrazin-2-yl;
6-membered rings having 3 heteroatoms such as: 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or 1,2,4-triazin-6-yl;
6-membered rings having 4 heteroatoms such as: 1,2,4,5-tetrazin-3-yl;
where, if appropriate, the sulfur of the abovementioned heterocycles may be oxidized to Sxe2x95x90O or S(xe2x95x90O)2 
and where a bicyclic ring system may be formed with a fused-on phenyl ring or with a C3-C6-carbocycle or with a further 5- or 6-membered heterocycle.
N-bonded heterocyclyl: a saturated, partially saturated or unsaturated 5- or 6-membered N-bonded heterocyclic ring which contains at least one nitrogen and, if appropriate, one to three identical or different heteroatoms selected from the following group: oxygen, sulphur or nitrogen, i.e., for example,
N-bonded 5-membered rings such as:
tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl, 2,5-dihydro-1H-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl, tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, 4,5-dihydro-1H-pyrazol-1-yl, 2,5-dihydro-1H-pyrazol-1-yl, 2,3-dihydro-1H-pyrazol-1-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl, 4,5-dihydro-1H-imidazol-1-yl, 2,5-dihydro-1H-imidazol-1-yl, 2,3-dihydro-1H-imidazol-1-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,4-xcex944-oxadiazolin-2-yl, 1,2,4-xcex942-oxadiazolin-4-yl, 1,2,4-xcex943-oxadiazolin-2-yl, 1,3,4-xcex942-oxadiazolin-4-yl, 1,2,4-xcex945-thiadiazolin-2-yl, 1,2,4-xcex943-thiadiazolin-2-yl, 1,2,4-xcex942-thiadiazolin-4-yl, 1,3,4-xcex942-thiadiazolin-4-yl, 1,2,3-xcex942-triazolin-1-yl, 1,2,4-xcex942-triazolin-1-yl, 1,2,4-xcex942-triazolin-4-yl, 1,2,4-xcex943-triazolin-1-yl, 1,2,4-xcex941-triazolin-4-yl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, tetrazol-1-yl;
and also N-bonded 6-membered rings such as:
piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl, 1,2-dihydropyridin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl, tetrahydro-1,3-thiazin-3-yl, tetrahydro-1,4-thiazin-4-yl, tetrahydro-1,4-oxazin-4-yl, tetrahydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-thiazin-2-yl, 2H-3,6-dihydro-1,2-oxazin-2-yl, 2H-3,6-dihydro-1,2-thiazinoxazin-2-yl, 2H-3,4-dihydro-1,2-thiazin-2-yl, 2,3,4,5-tetrahydropyridazin-2-yl, 1,2,5,6-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-2-yl, 1,2,3,6-tetrahydropyridazin-1-yl, 3,4,5,6-tetrahydropyrimidin-3-yl, 1,2,3,4-tetrahydropyrazin-1-yl, 1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-1,4-thiazin-4-yl, 2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl, 4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl, 1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl, 1,4-dihydropyrimidin-1-yl or 3,4-dihydropyrimidin-3-yl, and also N-bonded cyclic imides such as: phthalimide, tetrahydrophthalimide, succinimide, maleimide or glutarimide.
All phenyl rings or heterocyclyl radicals and also all phenyl components in phenyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, phenylcarbonyl, phenylalkenylcarbonyl, phenoxycarbonyl, phenylaminocarbonyl and Nxe2x80x94(C1-C6-alkyl)-N-phenylaminocarbonyl or heterocyclyl components in heterocyclyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl, heterocyclylalkenylcarbonyl, heterocyclyloxycarbonyl, heterocyclylaminocarbonyl and Nxe2x80x94(C1-C6-alkyl)-N-heterocyclylaminocarbonyl, are, unless stated otherwise, preferably unsubstituted or carry one to three halogen atoms and/or a nitro group, a cyano radical and/or one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy substituents.
The compounds of the formula I according to the invention where R7=IIa are designated as compounds of the formula Ia, and the compounds of the formula I where R7=IIb are designated as Ib.
With respect to the use of the compounds of the formula I according to the invention as herbicides, the variables preferably have the meanings below, in each case on their own or in combination:
X is S(xe2x95x90O)2 or CR4R5;
R1 is nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl or C1-C6-haloalkylsulfonyl;
R3 is hydrogen;
R4, R5 are hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl or C1-C6-haloalkylsulfonyl; or
R4 and R5 together form an xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94Sxe2x80x94 or xe2x80x94Oxe2x80x94(CH2)nxe2x80x94 chain which may be substituted by one to three radicals selected from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
R4 and R5 together form a xe2x80x94(CH2)pxe2x80x94 chain which may be interrupted by oxygen or sulfur and/or may carry one to four radicals selected from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
R4 and R5 together form a methylidene group which may be substituted by one to two radicals selected from the following group:
halogen, cyano, C1-C6alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
l is 0;
m is 2 to 4;
n is 1 to 5;
p is 2 to 5;
R7 is a compound IIa or IIb 
xe2x80x83where
R8 is halogen, OR10, SR10, SO2R11, OSO2R11, OPOR11R12, OPSR11R12, NR13R14, ONR14R14, N-bonded heterocyclyl or Oxe2x80x94(N-bonded heterocyclyl), where the heterocyclyl radical of the two lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R9 is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, di-(C1-C6-alkoxy)methyl, di-(C1-C6-alkylthio)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio)methyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl or C1-C6-haloalkoxycarbonyl; or
two radicals R9 which are attached to the same carbon together form an xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94Sxe2x80x94 or xe2x80x94Oxe2x80x94(CH2)nxe2x80x94 chain which may be substituted by one to three radicals selected from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
two radicals R9 which are attached to the same carbon together form a xe2x80x94(CH2)pxe2x80x94 chain which may be interrupted by oxygen or sulfur and/or may be substituted by one to four radicals selected from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
two radicals R9 which are attached to the same carbon together with this carbon form a carbonyl group; or
two radicals R9 which are attached to different carbons together form a xe2x80x94(CH2)nxe2x80x94 chain which may be substituted by one to three radicals selected from the following group:
halogen, C1-C6-alkyl, C1-C6-alkoxy, hydroxyl or C1-C6-alkoxycarbonyl;
R10 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C1-C20-alkylcarbonyl, C2-C6-alkenylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkynyloxycarbonyl, C1-C6-alkylthiocarbonyl, C1-C6-alkylaminocarbonyl, C3-C6-alkenylaminocarbonyl, C3-C6-alkynylaminocarbonyl, N,N-di-(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C3-C6-alkenyl)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C3-C6-alkynyl)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C1-C6-alkoxy)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C3-C6-alkenyl)-Nxe2x80x94(C1-C6-alkoxy)aminocarbonyl, Nxe2x80x94(C3-C6-alkynyl)-Nxe2x80x94(C1-C6-alkoxy)aminocarbonyl, di-(C1-C6-alkyl)aminothiocarbonyl, C1-C6-alkyl-carbonyl-C1-C6-alkyl, C1-C6-alkoxyimino-C1-C6-alkyl, Nxe2x80x94(C1-C6-alkylamino)imino-C1-C6-alkyl or N,N-di-(C1-C6-alkylamino)imino-C1-C6-alkyl, where the above-mentioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, hydroxycarbonyl, di-(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
xe2x80x83is phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, phenyl-C2-C6-alkenylcarbonyl or heterocyclyl-C2-C6-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 14 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R11, R12 are C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-6cycloalkyl, hydroxyl, C1-C6-alkoxy or di-(C1-C6-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, hydroxycarbonyl, di-(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
xe2x80x83are phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R13 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenyloxy or di-(C1-C6-alkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals selected from the following group: cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, hydroxycarbonyl, di-(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
xe2x80x83is phenyl, heterocyclyl, phenyl-C1-C6-alkyl or heterocyclyl-C1-C6-alkyl, where the phenyl or heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R14 is C1-C6-alkyl or C3-C6-alkenyl;
q 0 to 6.
Particular preference is given to compounds of the formula I, where the variables have the following meanings, in each case on their own or in combination:
X is S(xe2x95x90O)2 or CR4R5,
R1 is halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio or C1-C6-alkylsulfonyl;
in particular halogen such as chlorine or bromine, C1-C6-alkyl such as methyl or ethyl or C1-C6-alkoxy such as methoxy or ethoxy;
particularly preferably chlorine, methyl or methoxy;
R3 is hydrogen;
R4, R5 are hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy,
in particular hydrogen, C1-C6-alkyl or C1-C6-alkoxy;
particularly preferably hydrogen or C1-C6-alkyl such as methyl or ethyl; or
R4 and R5 together form an xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Sxe2x80x94 or xe2x80x94Sxe2x80x94(CH2)mxe2x80x94Sxe2x80x94 chain, which may be substituted by one to three radicals selected from the following group: C1-C4-alkyl or C1-C4-haloalkyl; or
R4 and R5 together form a xe2x80x94(CH2)pxe2x80x94 chain which may be substituted by one to four radicals selected from the following group:
halogen, C1-C4-alkyl or C1-C4-haloalkyl; or
R4 and R5 together form a methylidene group which may be substituted by one to two radicals selected from the following group:
halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
l is 0;
m is 2 to 4; in particular 2 or 3
p is 2 to 5;
R7 is a compound IIa or IIb 
xe2x80x83where
R8 is halogen, OR10, SR10, SO2R11, OSO2R11, NR13R14, ONR14R14, N-bonded heterocyclyl or Oxe2x80x94(N-bonded heterocyclyl), where the heterocyclyl radical of the two lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R9 is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, di-(C1-C6-alkoxy)methyl, di-(C1-C6-alkylthio)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio)methyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio or C1-C6-haloalkylthio, or
two radicals R9 which are attached to the same carbon together with this carbon form a carbonyl group;
R10 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C1-C20-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C1-C6-alkylaminocarbonyl, C3-C6-alkenylaminocarbonyl, N,N-di-(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C3-C6-alkenyl)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C1-C6-alkoxy)-Nxe2x80x94(C1-C6-alkyl)aminocarbonyl, Nxe2x80x94(C3-C6-alkenyl)-Nxe2x80x94(C1-C6-alkoxy)aminocarbonyl, di-(C1-C6-alkyl)aminothiocarbonyl or C1-C6-alkylcarbonyl-C1-C6-alkyl, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, hydroxycarbonyl, di-(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6cycloalkyl;
xe2x80x83is phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, heterocyclyloxycarbonyl or heterocyclyloxythiocarbonyl, where the phenyl and the heterocyclyl radical of the 12 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R11, R12 are C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-cycloalkyl, hydroxyl, C1-C6-alkoxy or di-(C1-C6-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, hydroxycarbonyl, di-(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
xe2x80x83are phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R13 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenyloxy or di-(C1-C6-alkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals selected from the following group:
cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, hydroxycarbonyl, di-(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
xe2x80x83is phenyl, heterocyclyl, phenyl-C1-C6-alkyl or heterocyclyl-C1-C6-alkyl, where the phenyl or heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R14 is C1-C6-alkyl or C3-C6-alkenyl;
q is 0 to 6.
Particular preference is given to compounds of the formula I, where
R4 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
particularly preferably hydrogen, C1-C6-alkyl such as methyl or ethyl or C1-C6-alkoxy such as methoxy or ethoxy;
R5 is hydrogen or C1-C6-alkyl; particularly preferably hydrogen or methyl; or
R4 and R5 together form an xe2x80x94Oxe2x80x94(CH2)2xe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)3xe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)2xe2x80x94Sxe2x80x94, xe2x80x94Oxe2x80x94(CH2)3xe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)2xe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)3xe2x80x94Sxe2x80x94, xe2x80x94(CH2)2xe2x80x94, xe2x80x94(CH2)4xe2x80x94 or xe2x80x94(CH2)5xe2x80x94 chain which may be substituted by one to three C1-C4-alkyl or C1-C4-haloalkyl radicals; or
R4 and R5 together form a methylidene group which may be substituted by a radical selected from the following group:
halogen such as chlorine or bromine, C1-C6-alkyl such as methyl or ethyl, C1-C6-haloalkyl such as chloromethyl, fluoromethyl, dichloromethyl, difluoromethyl or trifluoromethyl, C1-C6-alkoxy such as methoxy or ethoxy.
Very particular preference is given to the compounds of the formula I, where
R4 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
particularly preferably hydrogen, C1-C6-alkyl such as methyl or ethyl or C1-C6-alkoxy such as methoxy or ethoxy;
R5 is hydrogen or C1-C6-alkyl;
particularly preferably hydrogen or methyl.
Likewise, particular preference is given to compounds of the formula I, where
R9 is nitro, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, di-(C1-C6-alkoxy)methyl, di-(C1-C6-alkylthio)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio)methyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsufinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl or C1-C6-haloalkoxycarbonyl; or
two radicals R9 which are attached to the same carbon together form an xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Oxe2x80x94, xe2x80x94Oxe2x80x94(CH2)mxe2x80x94Sxe2x80x94, xe2x80x94Sxe2x80x94(CH2)mxe2x80x94Sxe2x80x94 or xe2x80x94Oxe2x80x94(CH2)nxe2x80x94 chain which may be substituted by one to three radicals selected from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
two radicals R9 which are attached to the same carbon form a xe2x80x94(CH2)pxe2x80x94 chain which may be interrupted by oxygen or sulfur and/or may be substituted by one to four radicals selected from the following group:
halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl; or
two radicals R9 which are attached to the same carbon together with this carbon form a carbonyl group.
Very particular preference is given to compounds of the formula I, where
R9 is nitro, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, di-(C1-C6-alkoxy)methyl, di-(C1-C6-alkylthio)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio)methyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsufinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl or C1-C6-haloalkoxycarbonyl; or
two radicals R9 which are attached to the same carbon together with this carbon form a carbonyl group.
Likewise, particular preference is given to the compounds of the formula I, where
R8 is NR13R14 or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy.
Likewise, particular preference is given to the compounds of the formula I, where
R8 is SR10, NR13R14 or N-bonded heterocyclyl, where the heterocyclyl radical may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy.
Very particular preference is given to compounds of the formula I, where
R8 is NR13R14 or tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl, 2,5-dihydro-1H-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl, tetrahydroisoxazol-2-yl, tetrahydrothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,4-triazol-1-yl, tetrazol-1-yl, piperidin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, tetrahydro-1,4-oxazin-4-yl, tetrahydro-1,2-oxazin-2-yl, succinimide, maleinimide or glutarimide, where the abovementioned heterocycles may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, such as methyl or ethyl, C1-C4-haloalkyl such as chloromethyl, difluoromethyl or trifluoromethyl, C1-C4-alkoxy such as methoxy or ethoxy or C1-C4-haloalkoxy such as difluoromethoxy or trifluoromethoxy.
Very particular preference is furthermore given to the compounds of the formula Ia.
Likewise, very particular preference is given to the compounds of the formula Ia where the variables are as defined below, in each case on their own or in combination:
X is S(xe2x95x90O)2 or CR4R5;
R1 is halogen or C1-C6-alkyl;
in particular chlorine, bromine or C1-C4-alkyl;
particularly preferably chlorine or methyl;
R3 is hydrogen;
R4 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy;
in particular C1-C6-alkyl or C1-C6-alkoxy;
particularly preferably methyl or methoxy;
R5 is hydrogen or C1-C6-alkyl;
in particular hydrogen or methyl;
1 [sic] is O;
R8 is halogen, OR10, SR10, SO2R11, NR13R14 or N-bonded heterocyclyl, where the heterocyclyl radical may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R9 is C1-C6-alkyl, such as methyl or ethyl;
in particular methyl; or
two radicals R9 which are attached to the same carbon form, together with this carbon, a carbonyl group;
R10 is C1-C6-alkyl, C3-C6-alkenyl or C3-C6-haloalkenyl, where the alkyl radical may be partially or fully halogenated and/or may carry one to three of the following groups:
C1-C4-alkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
xe2x80x83phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl or phenylcarbonyl, where the five lastmentioned radicals may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxy;
R11 is C1-C6-alkyl, C3-C6-alkenyl or C3-C6-haloalkenyl, where the alkyl radical may be partially or fully halogenated and/or may carry one to three of the following groups:
C1-C4-alkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
xe2x80x83phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl or phenylcarbonyl, where the five lastmentioned radicals may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxy; in particular C1-C6-alkyl or phenyl which may be partially or fully halogenated;
R13 is C1-C6-alkyl, such as methyl or ethyl;
R14 is C1-C6-alkoxy, such as methoxy or ethoxy;
q is from 0 to 6.
Particular preference is given to the compounds of the formula Ia where:
R8 is halogen, OR10, SR10, SO2R11, NR13R14, 4-morpholinyl, 2-tetrahydroisoxazolyl, 1-pyrrolidinyl or 1-(1,2,4-triazolyl).
Extraordinary preference is given to the compounds of the formula Ia1 and Ib1 (xe2x89xa1I where X=CR4R5 and l, q=0), in particular to the compounds Ia1.1 to Ia1.342 and the compounds Ib1.1 to Ib1.342, where the radical definitions R1 to R9, l and q not only in combination with one another, but in each case also on their own, have a particular meaning for the compounds according to the invention.
Furthermore, extraordinary preference is given to the following cyclohexenonedioxothiochromanoyl derivatives of the formula I:
The compounds of the formulae Ia2 and Ib2, in particular the compounds Ia2.1 to Ia2.342 and the compounds Ib2.1 to Ib2.342 which differ from the compounds Ia1.1 to Ia1.342 and Ib1.1 to Ib1.342, respectively, in that (R9)q is xe2x80x9c5,5-dimethylxe2x80x9d. 
The compounds of the formulae Ia3 and Ib3, in particular the compounds Ia3.1 to Ia3.342 and the compounds Ib3.1 to Ib3.342 which differ from the compounds Ia1.1 to Ia1.342 and Ib1.1 to Ib1.342, respectively, in that (R9)q is xe2x80x9c5-methylxe2x80x9d. 
The compounds of the formulae Ia4 and Ib4, in particular the compounds Ia4.1 to Ia4.342 and the compounds Ib4.1 to Ib4.342 which differ from the compounds Ia1.1 to Ia1.342 and Ib1.1 to Ib1.342, respectively, in that (R9)q is xe2x80x9c4,4-dimethylxe2x80x9d. 
The compounds of the formulae Ia5 and Ib5, in particular the compounds Ia5.1 to Ia5.342 and the compounds Ib5.1 to Ib5.342 which differ from the compounds Ia1.1 to Ia1.342 and Ib1.1 to Ib1.342, respectively, in that (R9)q is xe2x80x9c6,6-dimethylxe2x80x9d. 
The compounds of the formulae Ia6 and Ib6, in particular the compounds Ia6.1 to Ia6.342 and the compounds Ib6.1 to Ib6.342 which differ from the compounds Ia1.1 to Ia1.342 and Ib1.1 to Ib1.342, respectively, in that (R9)q is xe2x80x9c4,4,6,6-tetramethyl-5-oxoxe2x80x9d. 
The compounds of the formulae Ia7 and Ib7, in particular the compounds Ia7.1 to Ia7.342 and the compounds Ib7.1 to Ib7.342 which differ from the compounds Ia1.1 to Ia1.342 and Ib1.1 to Ib1.342, respectively, in that (R9)q is xe2x80x9c6-methylxe2x80x9d. 
The compounds of the formulae Ia8 and Ib8, in particular the compounds Ia8.1 to Ia8.342 and the compounds Ib8.1 to Ib8.342 which differ from the compounds Ia1.1 to Ia1.342 and Ib1.1 to Ib1.342, respectively, in that (R9)q is xe2x80x9c5-hydroxy-4,4,6,6-tetramethylxe2x80x9d. 
Extraordinary preference is also given to the compounds of the formulae Ia9 and Ib9 (xe2x89xa1I where X=SO2, R1=CH3, R3=H and l=0), in particular to the compounds Ia9.1 to Ia9.456 and Ib9.1 to Ib9.456 where the radical definitions R1 to R9, l and q not only in combination with one another, but in each case also on their own, have a particular meaning for the compounds according to the invention.
Furthermore, extraordinary preference is given to the compounds Ia10 and Ib10, in particular to the compounds Ia10.1 to Ia10.456 and Ib10.1 to Ib10.456, which differ from the compounds Ia9.1 to Ia9.456 and Ib9.1 to Ib9.456, respectively, in that R1 is chlorine. 
Likewise, extraordinary preference is given to the compounds Ia11 and Ib11 in particular to the compounds Ia11.1 to Ia11.456 and Ib11.1 to Ib11.456, which differ from the compounds Ia9.1 to Ia9.456 and Ib9.1 to Ib9.456, respectively, in that R1 is methoxy. 
Furthermore, extraordinary preference is given to the compounds Ia, in particular to the compounds Ia1 to Ia11, and to the embodiments mentioned in each case.
The cyclohexenonedioxothiochromanoyl derivatives of the formula I can be obtained by various routes, for example by the following processes:
A. Preparation of the compounds of the formula I where R8=halogen by reaction of cyclohexanedione derivatives of the formula III with halogenating agents: 
Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N,N-dimethylammonium chloride, oxylyl bromide, phosphorus oxybromide etc.
The starting materials are usually employed in equimolar amounts. However it can also be advantageous to employ one component or the other in excess.
Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or mixtures of these. The reaction can also be carried out neat.
The reaction temperature is usually in the range from 0xc2x0 C. to the boiling point of the reaction mixture.
Work-up to afford the product can be carried out in a manner known per se.
B. Preparation of compounds of the formula I where R8=OR10, OSO2R11, OPOR11R12 or OPSR11R12 by reaction of cyclohexanedione derivatives of the formula III with alkylating, sulfonylating or phosphonylating agents IVxcex1, IVxcex2, IVxcex3 or IVxcex4. 
L1 is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, hetaryl, for example imidazolyl, carboxylate, for example acetate, or sulfonate, for example mesylate or triflate, etc.
The compounds of the formula IVxcex1, IVxcex2, IVxcex3 or IVxcex4 can be employed directly, such as, for example, in the case of the carbonyl halides, or be generated in situ, for example activated carboxylic acids (using carboxylic acid and dicyclohexylcarbodiimide, etc.).
The starting materials are usually employed in equimolar amounts. However it can also be advantageous to employ one component or the other in excess.
It may be advantageous to carry out the reactions in the presence of a base. It is advantageous to employ the starting materials and the base in equimolar amounts. In certain cases, an excess of base, for example 1.5 to 3 molar equivalents, may be advantageous.
Suitable bases include tertiary alkylamines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal bicarbonates, such as sodium bicarbonate and potassium bicarbonate, alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, or alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine or pyridine.
Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide or esters, such as ethyl acetate, or mixtures of these.
The reaction temperature is usually in the range from 0xc2x0 C. to the boiling point of the reaction mixture.
Work-up to afford the product can be carried out in a manner known per se.
C. Preparation of compounds of the formula I where R8=OR10, SR10, POR11R12, NR13R14, ONR14R14, N-bonded heterocyclyl or Oxe2x80x94(N-bonded heterocyclyl) by reaction of compounds of the formula I where R8=halogen, OSO2R11 (Ixcex1) with compounds of the formula Vxcex1, Vxcex2, Vxcex3, Vxcex4, Vxcex5, Vxcex7 or Vxcex8, if appropriate in the presence of a base or with prior salt formation. 
The starting materials are usually employed in equimolar amounts. However it can also be advantageous to employ one component or the other in excess.
It may be advantageous to carry out the reactions in the presence of a base. It is advantageous to employ the starting materials and the base in equimolar amounts. In certain cases, an excess of base, for example 1.5 to 3 molar equivalents based on Ia and/or Ib (where R8=halogen), may be advantageous.
Suitable bases include tertiary alkylamines, such as tertiary alkylamines [sic], such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal bicarbonates, such as sodium bicarbonate and potassium bicarbonate, alkali metal alkoxides, such as sodium methoxide, sodium methoxide [sic], potassium tert-butoxide, or alkali metal hydrides, for example sodium hydride. Preference is given to using sodium hydroxide or potassium tert-butoxide.
Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or mixtures of these.
In general, the reaction temperature is in the range from 0xc2x0 C. to the boiling point of the reaction mixture.
Work-up to give the product can be carried out in a manner known per se.
D. Preparation of compounds of the formula I where R8=SOR11, SO2R11 by reaction of compounds of the formula I where R8=SR11 (Ixcex2) with an oxidizing agent. 
Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxoacetic acid, trifluoroperoxoacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst such as tungstate.
The starting materials are usually employed in equimolar amounts. However it can also be advantageous to employ one component or the other in excess.
Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxan, polar aprotic solvents, such as acetonitrile or dimethylformamide, or esters, such as ethyl acetate, or mixtures of these.
The reaction temperature is usually in the range from 0xc2x0 C. to the boiling point of the reaction mixture.
Work-up to afford the product can be carried out in a manner known per se.
Depending on the reaction conditions, the compounds Ia, Ib or mixtures thereof can be formed. The mixtures can be separated by classic separation methods, such as, for example crystallization, chromatography, etc.
The cyclohexanedione derivatives of the formula III are known or can be prepared by processes known per se (for example DE 19 532 311), for example by reacting cyclohexanones of the formula VI with an activated benzoic acid VIIa or a benzoic acid VIIb, which is preferably activated in situ, to give the acylation product, and subsequent rearrangement. 
L2 is a nucleophilically replaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, etc.
The activated benzoic acid VIIa can be employed directly, as in the case of the benzoyl halides, or be generated in situ, for example using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester, 2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.
It may be advantageous to carry out the acylation reaction in the presence of a base. It is advantageous to employ the starting materials and the auxiliary base in equimolar amounts. In certain cases, a small excess of the auxiliary base, for example 1.2 to 1.5 molar equivalents based on VII, may be advantageous.
Suitable auxiliary bases include tertiary alkylamines, pyridine and alkali metal carbonates. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide or esters, such as ethyl acetate, or mixtures of these.
If benzoyl halides are employed as activated carboxylic acid component, it may be advantageous to cool the reaction mixture to 0-10xc2x0 C. when adding this reactant. Stirring is then continued at 20-100xc2x0 C., preferably at 25-50xc2x0 C., until the reaction has ended. Work-up is carried out in a conventional manner; for instance, the reaction mixture is poured into water and the product of value is extracted. Suitable solvents for this purpose are in particular methylene chloride, diethyl ether and ethyl acetate. After drying of the organic phase and removal of the solvent, the crude ester can be used for the rearrangement without any further purification.
The rearrangement of the esters to give the compounds of the formula III is advantageously carried out at from 20 to 100xc2x0 C. in a solvent and in the presence of a base using, if appropriate, a cyano compound as catalyst.
Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, dioxan, ethyl acetate, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxan.
Suitable bases are tertiary amines such as triethylamine, aromatic amines such as pyridine or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in equimolar amounts or up to a four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonate, preferably in double the equimolar amount based on the ester.
Suitable cyano compounds are inorganic cyanides, such as sodium cyanide or potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin and trimethylsilyl cyanide. They are employed in an amount of from 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example in an amount of from 5 to 15, preferably 10, mol percent, based on the ester.
Work-up can be carried out in a manner known per se. The reaction mixture is acidified, for example with dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the resulting precipitate is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, dried and concentrated.
The benzoyl halides of the formula VIIa (where L2=Cl, Br) can be prepared in a manner known per se by reacting the benzoic acids of the formula VIIb with halogenating agents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride or oxalyl bromide.
The benzoic acids of the formula VIIb can be prepared in a known manner from the corresponding esters by acid or basic hydrolysis.